Synthesis
1-(2-Chloroethoxy)-4-nitrobenzene was synthesized as follows: cesium carbonate (28.7 mmol) was added to a solution of 4-nitrophenol (28.7 mmol) in anhydrous ethanol (15 mL), followed by 1-bromo-2-chloroethane (86.2 mmol). The reaction mixture was heated to reflux at 80 °C for 8 hours. Upon completion of the reaction, the mixture was cooled, the reaction was quenched with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give an orange residue. Grinding of the residue with ethanol (EtOH) gave 1-(2-chloroethoxy)-4-nitrobenzene in 66% yield. Mass spectrum (MS) (m/z): (M+1)+ 202.2.
References
[1] Patent: WO2007/38669, 2007, A2. Location in patent: Page/Page column 170
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 16, p. 4981 - 4991
[3] Patent: WO2005/68452, 2005, A1. Location in patent: Page/Page column 41
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1637 - 1648
[5] Patent: WO2004/5282, 2004, A1. Location in patent: Page 39
